Process of making benzyl chlorid from toluol.



C. ELLIS.

PROCESS OF MAKING BENZYL CH LOR|D FROM 'TOLUOL. APPLICATION FILED AUG.I6. 19:12.

WITNESSES ATTORNEYS Z '0 all whom it may concern:

UNITED, STATES PATENT OFFICE.

PROCESS OF MAKING IBENZYL CHLORID FROM TOLUOL.

Specifieation-of Letters Patent.

'CARLETCN ELLIS, or MCNTC'LAIR, NEW JERSEY, assmnon 'I'o CHADELOID CHEMICAn COMPANY, on NEW YQRK, N. Y A CORPORATION or WEST VIRGINIA.

Patented Oct. 24, 1916.

' Application filed August 16, 1912. Serial No. 715,325.

Be it known that I, CARLEroN ELLIS, a citizen of the United States, and resident of Montclair, Essex county, New Jersey, have made a certain new and useful Invention Relating to Processes of Making Benzyl Chlorid from Toluol, of-which the follow ing is a specification, taken in connection tinuous circulation of an excess of toluol' with the accompanying drawing; which forms part of the same.

This invention relates to the manufacture of benzyl chlorid from toluol by the conthrough the apparatus, in which an excess of toluol vapor is produced and acted upon by chlorin at an elevated temperature to promote the side chain chlorination preferably under gradually increasing temperature conditions and in the presence of actinic action to promote the chlorination. The benzyl chlorid may then be condensed and removed and the remaining vaporous material subsequently condensed and the hydrochloric acid substantially eliminated before the remaining toluol is returned to the still for retreatment.

In the accompanying drawing an illustrative form of apparatus for carrying out this process is shown somewhat diagrammatically and as indicated the still 1 may be provided with a suitable dephlegmator 2 soas to vaporize the toluol delivered to the treating conduit or chamber 3 to which chlorin is also supplied as through the chlorin pipe 9 in'which a suitable valve 10 may be provided to regulate the amount of chlorin. The chlorin may be preheated to the desired extent by a suitable heater, such as 31, so that the chlorin is brought up to the desired temperature before coming into contact with the toluol vapor. The treating chamber may be heated in any way as by arranging it within an air heater or other heating jacket 4 to which hot air may be supplied as through the inlet 5 so as to pass along through the heating jacket before be ing discharged from the outlet 6. Any de sired number of baflies or partitions 28 may be formed within this heating jacket, pref erably having apertures or passages adjacent their lower portions which arecontrolled by suitable regulating valves or dampers such as 8 to insure the desired heat distribution throughout the jacket, part of the heated air or other medlum being, 1f desired, discharged through intermediate dis- If desired, the

phorous .pentachlorid and so forth may be used to advantage in this. way where the temperature is not undesirably high.' The preliminary portions of; the conduit orchamber may also be filled more or less with suitable acceleratmg or catalyzing material such as fragments-of pumice, porcelain or glass beads and so forth as indicated at 30,

these materials-considerably promoting the reaction desired.

The treated vapors entering the pipe 11 comprise benzyl chlorid and hydrochloric acid gas which arethe products of this side chain chlorination and also the large proportion of unchanged toluol vapor, the toluol vapor being preferably 'only converted in this treating chamber to the extent of a quarter or a half during each passage. lhese mixed vapors are preferably passed through a dephlegmatorto substantially eliminate the benzyl chlorid therefrom and the dephlegmator 12 is diagrammatically indicated as being provided with a cooling jacket 14 in which superheated steam, air or other vapor is circulated as through the valved j acket pipe 15, the drip and discharge material being discharged through the pipe 16. .In this way the acket may be maintained at the desired temperature about 150 degrees C. giving good results in general commercial operation, the

dephlegmator by means of conductive partitions or otherwise being thus maintained at a temperature slightly below the condensing temperature of benzyl chlorid which is about" 179 degrees (1, although the jacket temperature may of course be varied within considerable limits, depending upon the construction of the dephlegmator, the amount of material condensed and so forth. The

w condensed benzyl chlorid'must be removedcontinually or from time to time through the trapped discharge pipe 13. The remaining vapor niav pass from the dephlegmator 5 through the pipe 17 mto a suitable toluol condenser 18 provided with the water or other cooling jacket 19 in which the circulation i is maintained through the valved inlet 20 and outlet 21. The toluol is condensed with substantial completeness in this way and flows through the pipe back into the still, the hydrochloric acid gasbeing eliminated with substantial complete ness by the interposed separating chamber 523 from which the gas is allowed to discharge through the valved pipe 2% com municating with condensing or utilizing devices of the character desired. Additional toluol or material largely consisting thereof 0 may be continuously supplied to the system,

as through the valved inlet 26 communicating adjacent the trapped portion of the pipe 25 leading to the still 1.

Having described this invention in con- 5 nection with a number of illustrative em- 0-point of toluol and gradually increasing the temperature of the mixed Vapors while in said zone,in condensing and separating 'benzyl chlorid from the treated vapors, 1n

condensing toluol in the remaining vaporous material and separating hydrochloric acid "as therefrom and in continuously supplymg additional toluol material thereto before again vaporizing the same.

2. The process of making benzyl chlorid which comprises mixing toluol vapor and chlorin gas, in subjecting the mixed vapors to heat in a heat zone at temperatures independent of and above the boiling point of toluol and in increasing the temperature of said vapors while in said heatin zone.

3. The process ofmaking benzy "chlorid which comprises 'mixing toluol vapor and heated chlorin gas in suflicient amount to combine with part of said toluol vapor, in passing the mixed vapors through a zone of heat maintained at a temperature independent of and above the boiling point of toluol to form benzyl chlorid and hydrochloric acid and in condensing and separating benzyl chlorid from the treated vaporous material.

4. The process of making benzyl chlorid which comprises mixing toluol vapor and chlorin gas and in passing the mixed vapors into and through a zone of heat maintained at a temperature independent of and above the boiling point of toluol.

5. The process of makin benzyl chlorid which comprises continuous y mixing toluol vapor and chlorin gases, in passing the mixture as a continuous current from the vaporizing space into an elongated heating zone wherein the temperature of the gaseous current is progressively raised to a point substantially above theboiling 'point of- 

